


Ruined While You Sleep

by MoonlightIcarus



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Bad BDSM Etiquette, Bottom Dean Winchester, Catheters, Cheating, Come Marking, Condoms, Crack, Dark Sam Winchester, Dildos, Dom Sam Winchester, Emotional Manipulation, Facials, Filthy, Gaslighting, Hand Jobs, Handcuffs, I Wrote This Instead of Sleeping, Infidelity, Jock Straps, M/M, No Incest, Non-Consensual Drug Use, Non-Consensual Somnophilia, Non-Consensual Voyeurism, Possessive Behavior, Possessive Sam Winchester, Prostate Massage, Rape/Non-con Elements, Restraints, Sam Winchester Has a Large Cock, Smut, Top Sam Winchester, Underwear Kink, flesh light
Language: English
Status: Completed
Published: 2020-01-19
Updated: 2020-01-24
Packaged: 2021-02-27 09:09:17
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 12,134
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22314586
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: Sam Wesson comes home after a night at his favorite local BDSM club and finds his roommate Dean passed out drunk on his bed without any pants on and his hole stretched wide open after his boyfriend Castiel left for the night.He uses some of his toys to make things appear worse then they really were so that when Dean wake ups Sam gets to see the look in his eyes. And give some strong suggestions to make the man his.Now proofread and re edited.
Relationships: Castiel/Dean Winchester, Dean Smith/Sam Wesson, Dean Winchester/Sam Winchester
Comments: 27
Kudos: 172





	1. Chapter 1

Tonight hasn't been what Sam was expecting but it wasn't a total waste. There wasn't anyone at the club he wanted to fuck, but that was really because the only person he wanted to fuck was his roommate.

Dean Wesson was a sex muse. Some of the best scene ideas Sam came up with over the last few months were things he'd wanted to do to Dean, but he was forced to settle with using them on his random sub of the night down at the club.

He would have screwed Dean if he could, but unfortunately the man had been in denial about being bisexual for the longest time, and the moment he finally accepted it he already had a boyfriend before Sam could make a move. It was just unfair in how it turned out. He resisted making a move for nearly years, and then before he even knows what's happening Dean gets someone else to shove their dick up his hole.

While he may not have had any confirmation that Dean was a bottom, he had more than eight functioning brain cells, and he could deduce that Dean would never top anyone. Even the women he dated probably just pegged him, instead of him actually getting to fuck them. 

That being said tonight was a wash when it came to ignoring his desire for his roommate. He had watched someone fuck a sub who was fully restrained and begged to cum through out the whole scene (he never did get to cum). After that he collected more than a dozen used condoms for the scene he was planning for tomorrow night. 

That was an interesting conversation; asking men for their used condoms, but these were members of a BDSM club so he just excused it as something for a scene and they handed them over without any further questions. Now he was carrying them inside of a cooler into his house. 

And the lights were on....at 3:42 in the morning on a Friday (technically Saturday since it was after midnight) night. Dean had stayed up this late before, but usually he'd text Sam a heads up letting him know to steer clear while he was having wild and crazy sex for the night. It was part of their unspoken agreement as room mates: don't get tangled up in each others sex lives, even though all he wanted to do was combine their separate sex lives into one.

Maybe the good thing to do would have been to turn around and rent a hotel room for the night, but Dean didn't show him any courtesy so he wouldn't show him any in return. It was only fair to do that.

After the door swung open the living room Sam looked around, and it was half like what he expected. It was messier than a frat house during finals week, but their weren't any people at all. Not a single one. There were traces of them from the large number of beer cans and solo cups strewn about the living room, to the tracks of mud and shoe prints spanning across the hardwood floors.

The couch was out of place, the tv was on the ground, but miraculously it was still in one piece and appeared to be free of any damage, and the standing lamp was tipped over. Foreseeing moments like these were exactly why he needed a house with hardwood flooring; it was so much easier to clean up a large mess, but he wouldn't be the one doing it, that joy was going to be on Dean.

Sam walked through the trashed living room and made it through the less dirty, but still a mess hallway over to Dean's room, only stopping to place the small cooler in his bedroom so he didn't have to hold it the whole time he cussed Dean out for his stupidity.

He threw the door open fully intending on waking him up with the bang, but when he flicked the light switch on Dean was still asleep...and bottom less. He still had a Henley on but from where he could see Dean was lying on his stomache with his lower half completely bare. 

This was another time he should have turned around and walked away from the situation, but he'd wanted to see Dean's ass up close and personal for the whole five years they'd been friends and two year that they'd been roommates, so he was going to seize the moment.

During the approach he got a better view of how Dean was laid out. One of his legs was hitched up exposing his stretch out hole, showing it off to the mostly empty room. Sam was so tempted by the sight that he couldn't stop himself from touching it. He just lightly ghosted his finger over it and got no reaction from Dean. Then he pushed down harder and still nothing. Finally he inserted his index finger and when the only acknowledgment he received was a slight twitch of Dean's nose he decided to be a little devious. 

He'd earned the right to do this, to set up Dean Smith like his perfect sub. But, if it truly was his only chance then he was going to make it perfect for his desires.

He returned to his room and opened up the toy chest he kept in the back of his closest, pulling out some black hand mitts, a set of police grade handcuffs, his largest bottle of lube (grape flavored), his softest pair of nipple clamps, and a black collar he kept on standby in case he ever needed one, and in this situation it certainly qualified as a necessity. Sam also grabbed the cooler on the way out, because this took presidence over the scene he was planning. That could happen at anytime, but an opportunity like this may only fall into his lap once.

Coming back into Dean's room he secured Dean's hands behind his back in the cuffs and then placed the mitts on them. Now his hands were just two large black ovals that were entirely useless to him, and his arms were stretched out along the length of his back.

Sam was happy to take his time. This wasn't the first time he'd found Dean passed out after drinking, and from prior experience he wouldn't wake up to anything except his own volition at sometime around noon the following day.

He had to work a little to fasten the collar around Dean's neck, but he managed it and secured it tight enough to rub against Dean's throat if he moved around, but loose enough to not consistently constrict his airways. Sam chose to wait on the nipple clamps, because he had several plans for Dean's front and it would be more efficient to do them all at once.

He returned to Dean's ass. It looked fuckable as all hell, but the more he stared at it the more he wanted to do a myriad of things to it that didn't involve his dick. Dean needed to look and feel owned. Sam could just cum on his face later to sooth his possessiveness, right now he wanted to add to the lie he was building for Dean to wake up to in the morning. 

He popped the cap off his bottle of lube and poured it all over Dean's ass and let the excess drip down his thighs and onto the bed. It was held open over this crack and it fell down his balls and dick as well. 

Now it was time to stretch him out more. His hole had clearly been used, but Sam needed it wrecked. He coated his fingers and started straight away with two of them, Dean had no chance of waking up soon so he could be harsher than he would have been if Dean was cognizant.

He added more lube at three fingers and then even more at four. His ass needed to hurt like he'd been gangbanged. 

A dildo would help with that and with his constant snooping through Dean's things he knew exactly where Dean stored his dildo. It was in the shoebox under his bed, as obvious a spot as any to store a sex toy, but he didn't like Dean for his brains even if he was a pretty smart man.

The box slid out from beneath its hiding place and Sam was overjoyed to see the long pink toy. It was riveted (yeah Dean knew he was gay as fuck long before he admitted it if his first and only sex toy was a dildo covered in small bumps to help stimulate his ass). It was lined up then shoved into that opening quickly. He still had lots to do and even if Dean wouldn't be awake for hours Sam still needed to sleep.

A few full thrusts were done and then Sam started to add his fingers again. He wanted to wake up to Dean moaning from pain lighting up across his body, so his relatively inexperienced anus was the first thing to tackle. 

He got a whole extra four fingers up inside Dean before he pulled both his hand and the dildo out. Now was the time to stuff his ass full of lube. He only had so much cum left over from the used condoms and those were going to serve a different purpose so lube would have to do as a substitute for the copious amounts of cum he wanted Dean to believe was filling his ass.

He spooned it in with his hand and the forced it deeper I side with the dildo, repeating the process until he was sure it would leak out of his ass slowly thought the night and continue to do it when Dean first sat up tomorrow morning after he was freed.

The dildo got pushed back into his ass, but it didn't fill him up like it had before with how stretched out he was, though it would still limit the flow of lube to just a light trickle.

Sam opened up the cooler and pulled out a few of the condoms rolling them inside out so he could rub them into Dean's skin. Three went into his hair, four on his ass, one on the mitts, and Sam even opened Dean's mouth so that he could rub two of them onto Dean's tongue, and even that didn't illicit a reaction out of him. This way he could wake up with the bitter taste of dried cum on his lips.

Then Sam rolled him onto his side and rubbed six loads into the messy bush of hair right above his cock, before pulling himself out and cumming on his stomache. The orgasm lacked the flair and finesse he desired, but that was being saved for when he came across Dean's face to finish it all off. 

As it were Dean's bush would be hard and crusty in the morning, sticking to his once again aching cock as it slowly softened over night.

While he had him on his side Sam applied the nipple clamps. He rucked up the Henley Dean was wearing and put them on delicately. These weren't the alligator clamps he preffered to use where he could tighten them to fit his current desire, but they were the most difficult to squirm out of and Dean would definitely do his fair share of squirming in the morning. Those nipples would still be enflamed and enlarged by daylight, just not to the extent Sam knew he could bring them to if he was allowed to fully indulge himself.

Finally it was time to paint that face. It had only been a few minutes, but Sam was ready to cum again, because Dean was just that fucking hot.

He started out frantic, the squelching from all the excess lube caused the wet sounds of his hand to reverberate through the room. He was focused on that slack open jaw where the cum he had smeared there earlier was still visible, and all he could think about was doing this again at a club or fucking Dean for hours and hours until he looked like this again.

"Oh, Dean." Sam whined and it was over. His cum landed along his eyebrow, nose, and lips, with some manging to drip down his cheek and land inside of his mouth.

Sam tucked himself away again and started to the spread out the rest of the used condoms along the bed and floor before he rolled Dean back onto his stomach with two condoms pinned under him, so Sam would be able to peel him off the mattress as his body stuck to it tomorrow.

For a final touch he went to the kitchen and grabbed the last pack of deer and seven more solo cups. He spilled the cans on the floor and poured a little into the cups before tipping them over or setting them on Dean's dresser, so it looked as if all his friends got drunk and fucked him relentlessly through the night. 

Finally he had about half a beer left and he poured it into Dean's hair and on his back. He would smell disgusting tomorrow and that would feed into the shame and guilt, Sam wanted him to feel while he "helped" to free him.

He took his cooler and left the bedroom for his own room. Then he stripped down and fell asleep as the aftermath of his two recent orgams hit him 

....

Just like he wanted he heard pained moans and please for help coming from the next room over. He wanted Dean to wait that extra little bit longer so he took his time dressing. He settled on his hot pink thong. It would hang low enough it the front to show off his well trimmed bush and the root of his cock, and then over that he put on white gym shorts. They had no waistband at all so they would hang even lower than the thong, but still outline his hard cock for Dean to see as Sam walked in on him. The shorts were only about five inches long at their longest point down the center, but the sides were cut much hiser up and they had slits on them exposing more of his skin, leaving nothing to the imagination. Honestly if Sam just stood with a less wide stance then they would have slipped right down his legs onto the floor. 

He would have looked less obscene walking in there with nothing on at all and that's what made this fun. Even while he was scantily clad Dean was wrapped up in sex toys and covered in various fluids so Sam by default would be more presentable than him

The door opened smoothly for him and Dean turned his head to face Sam. His eyes held an unspoken plea for help and the taller man obliged, taking in the way Dean was presented all over again as if he wasn't responsible for it.

He pulled Dean up into a sting position making him groan as the didlo was once again shoved fully into his ass. Sam then started with the nipple clamps. Dean moaned when they came off and after Sam set them down on the bed next to him he pressed his thumbs into the aching nubs.

"What do you think you're doing, Sammy?" Dean certainly sounded fucked out, but Sam knew he could make him sound even better.

"I'm checking to make sure Cas didn't do anything stupid last night when he put these on you." He needed to plant the seeds of doubt inside his head if he wanted to get Dean into his bed.

"Cas did this?" He sounded so much like he didn't want to believe it, but there existed some small part of him that thought it was true.

"Well I'm guessing it was him and like twenty other guys going by the numbers of used condoms around here." He paused to let the gravity of it sink in. "So either Cas was involved or you cheated on him in an orgy." He gently pushed Dean back down, and slowly started his pull on the dildo. Dean grunted or whined on each of the little bumps as they came out of him.

"I remember having him and a few guys over last night, but then it got really fuzzy. Maybe I shouldn't try to get blackout drunk anymore." He felt so betrayed. If Cass really did something like this to him, knowing he was too drunk to understand what he was agreeing to then what else would he try to get Dean to do?

"You've been doing it a lot more frequently since you met Cas and then with all this you may want to break it off for your own good." Now Sam was just the good friend who helped Dean in his time of need, and Cas was just the guy who used Dean and left him alone like this. "But I won't try to speak for you." If you make someone think something is their idea or their choice then they are more likely to go along with it. Sam learned that about manipulating people a long time ago.

The dildo finally came out and Sam moved to the mitts. It was a good thing Dean was too busy with his inner turmoil to question how sam knew exactly how to remove all of these sex toys. 

"He always seems so nice, but stuff like this..."

"If he knowingly did things that made you uncomfortable without consulting you I really do think you at least need some time away from him to think it over. Clear your head a bit." Just be supportive even if you want to pound him into the mattress at this very moment. "Space is good in a relationship."

"That seems like a good idea."

"I'm here for you pal." He had the mitts off and Dean was flexing his fingers wildly and openly now. Sam pretended to inspect the handcuffs before stating, "I'll need to grab my lock picking kit to get these off. I actually might have a skeleton key in there that could fit these so hopefully it won't take me too long. Just gimme a sec to go and get my stuff." 

"Okay." The dejection in his voice was slowly bleeding over into gratitude.

He left Dean on the bed, and he knew as he walked out the door Dean could see the top of his ass as it was exposed in his shorts. The rest of his ass was visible through the clear outline of the thin fabric. He was swaying in his steps for that little extra flair of overkill.

He slipped the key to the cuffs inside his lock picking set before returning and sitting in his previous spot next to Dean. He repeated the overly flirtatious walk, allowing his cock to bounce up and down with his strides.

""Here goes." He pretended to test the key before sliding it into place and rotating it to open up the cuffs and then it was repeated on the other side. They were thrown in along with all the other sex toys.

Dean let Sam sit him up and rest under that strong arm. From this angle Sam saw that Dean must have been turning in his sleep becuase he had some major bed head even after he had beer poured into it last night, and when he took a glance at Dean's crotch. His bush looked downright painful with how crusty it appeared. 

"You feeling okay."

"I'm doing better, Sammy. Thanks for the help." He sounded meek and exhausted.

"Its nothing." 

"No seriously. I don't know how I can repay you for helping me out." There was pleading in his tone, and that was something Sam could take advantage of.

"If you really want to thank me you could help me get rid of this morning wood."

He used his grip on Dean's head to angle his face down towards here his swollen membrane was throbbing in its confines. And, then Dean started to lean down towards Sam's lap all on his own.


	2. Chapter 2

**Summary for the Chapter:**

> Sam takes some baby steps to get what he wants.

**Notes for the Chapter:**

> So yeah, I thought I might only do one chapter for this fic but then people asked for another chapter, and I got more and more ideas so I'll be doing two more chapters and maybe more if inspiration hits me.

Dean pushed Sam's shorts and thong out of the way, letting the hard apendage spring up once it was free. He was pretty intimated by it. Sam easily had two inches on top of what Cas was packing and he usually struggled to even hold that down. Cas always told him to just do his best because he was in experienced but right now he left like he needed to make this the best blowjob Sam ever got or he would feel guilty that Sam had to untie him.

The head was wider than he was used to and already there was a drop of precum forming at the top of it. Dean sucked the tip into his mouth and Sam's hand fisted into the back if his messed up hair. Pushing and pulling on him slightly without evenle going far enough to choke him on it, even if hearing him choke would make this that much hotter. 

"Babysteps." Sam thought and he pushed Dean down that little bit more to help get his dick wet. The man looked like an absolute fucking whore dressed in only a henley stained with all the fluids from the previous night with his hole still dripping with lube. Fingering that loose sloppy mess would have been a cherry on top while Dean helplessly pleasured him.

His self restraint turned out to be unnecessary because Dean was choking himself on Sam's cock in an attempt to take more of it. Sam had never met someone who could take all of him on the first try, but Dean was sure giving it his all. He was unaware of how much he really was a little cock whore. Even without being told he was doing exactly what Sam wanted of him, like the good bitch that he was.

When Sam saw Dean's free hand move to his own crotch to pleasure himself while he gave a blowjob the knee jerk reaction was to smack it away because his pleasure was secondary to Sam's but again, "Baby Steps." He could have flipped Dean over and fucked his ass right then and there, but that would be sacrificing long term enjoyment for short term pleasure.

He could moan now. This was something pleasurable and that meant he could moan loudly without fear that Dean might hear him from the other room. Moaning made it easier to not thrust up into that mouth. Letting his own pleasure be known felt good even if he couldn't do all the things he'd dreamt of.

Paddles and canes, dildos and vibes, collars and ball gags, Dean would be a fine sub once he was addicted to cock like a good slut.

The effort he put in was equal to the joy Sam got from this. He'd been hard all morning so it didn't take a lot for him to finally push Dean down to where the head of his cock bumped the back of his throat and he began filling up his mouth with his release. He didn't let go of him until he was finished, pressing his dick against Dean's tongue when he finally pulled out.

"Thanks, Dean." he guided the other man back up into a sitting position and took in how the excess cum was leaking from his mouth and staining his lips. "I think a shower is a good idea. You small like beer and sex and I came home late last night and didn't get the chance to clean myself up."

"Okay, Sammy."

They took turns showering in the bathroom across from Dean's room. Sam, feigning to be a good well intentioned friend, let Dean go first. A follow up round of shower sex would have been ideal, but Dean was like a deer, you couldn't startle them or they'd run off to who knows where. Besides, there were other ways to amuse himself during Dean's shower.

The bathroom was adjacent to the garage and some time ago Sam had drilled a hole into the wall next to the shower. It was almost inperecptively small, and even after all this time Dean didn't know it was there. Sam used it to spy on Dean during his showers with his favoirte ones being the times Dean would jerk off in the shower and he was able to do the same thing on just the other side of the wall.

He repeatedly lathered up and scrubbed down his body. Those still swollen nipples brought a grunt out of his throat whenever his hands scrubbed over them. "If only he know how much pain and pleasure I could bring out of him with just those little nubs."

Dean began grunting when he scrubbed his bush clean. the dried up cum didn't turn to a liquid as the water hit it, instead it would need to be pulled out of the hair in large clumps, plucking pubic hairs as the deed was done. The faintest of sounds were heard from the action and not for the first time Sam wished the sound insilation wasn't so good so he could hear Dean whining. But, then he would have to watch his own noises so it would be a double edged sword.

Dean was agonizingly fingering his ass, attempting to get out what he believed to be loads upon loads of stranger's semen when it was nothing more than a large amount of grape flavored lube. He dug deep into his ass to clean himself, but there was some just too deep inside of him to reach it and eventually he gave and moved on to cleaning the rest of his body. The remainder would leak out of him slowly, driving him wild for the remainder of the day.

After shampooing his hair and rinsing it for the third time Dean shut off the water and got out of the shower. A towel was wrapped tightly around his waste and he left the bathroom to go get dressed. This was done without brushing his teeth meaning he still had the taste of Sam's cum on his tongue. A revelation Sam took great pleasure in.

Dean's bedroom door closed and Sam opened the garage door to sneak in and take his turn in the shower. The water was only lukewarm after Dean's liberal use of the hot water in his extended shower, but it was a small price for Sam to pay in proportion to the extensive show he was given.

Watching Dean had him hard again, and while he could have jerked off, he didn't. Being hard and having Dean see him like that while he was busy cleaning up his mess would be part of his punishment and it would aid in getting Dean's inhibitions around Sam out of the way.

He toweled dry and put back on his thong and shorts before walking to go talk to Dean about cleaning up the main room. Guiltily the other man agreed to it and Sam watched from the comfort of the undisturned armchair as Dean moved the furniture back into place and scrubbed the floors clear. 

Seeing Sam in so little clothing while he himself was fully dressed made him feel awkward and out of place, so he took off his jeans and flannel over shirt, and kept cleaning in just his boxer breifs and a tee shirt. Even that felt like too much and eventually he was on his hands and knees washing the floor in only his boxers while Sam groped his hard cock from the arm chair.

Seeing that ass jut out while he cleaned up his mess gave Sam ideas he didn't dare think about for too long or he'd be coming right then and there. A wet spot was forming at the back of deans boxers were the lube had finally managed to work it's way down and out of him. Either Dean was too distracted to notice it, or he was trying to avoid acknowledging it, because the wet stain continued to grow and the brunette did nothing about it.

"Dean keep cleaning, I'll go and make some lunch for us." Sam walked to the mostly cleaned kitchen to prepare something to eat.

Dean shouted at him from the other room."Not rabbit food, bitch." 

Sam shouted right back. "I'll make sandwiches, jerk." 

"Fine."

It was just ham and cheese subs with lettuce, tomato, and red onions on them, so he knew Dean was eating a vegetable. Until he could get Dean to agree to regular douching and enemas, Sam needed to assure that Dean was regular, so that his bowels didn't get in the way of their fun.

"Dean take a break and come eat."

There was no vocal response, but the sound of water running in the bathroom sink carried through the open door into the kitchen served as an indication that Dean was coming.

With the footsteps approaching the entrance Sam leaned across the length of the table to set the plates out on his and Dean's respective spots. His back was bowed and his ass was presented outward and his shorts had drooping down lower in the back fully exposing his ass to Dean. 

Now, the other man might think this was an invitation to fuck Sam and that assumption would be dead wrong. His ass was definitely worse than Dean's. It lacked the shape and bounce of his, and there wasn't that light layer of fat that would make it fun to play with as soon as he got his hands on it, but his ass was still all hard muscle. He wanted Dean to know that Sam had the ability to piston in and out of his ass like a machine, and that he would be moaning and desperate for his own pleasure every second thay they were together.

With the plates down Sam turn back to face the other man, and simultaneously adjusted his shorts in an obvious and entirely not subtle way. "So, you having fun?" The smarmy ass was pulling a Spinal Tap and dialing it up to eleven. Dean couldn't even manage to make eye contact with him.

"No, I'm not." He was out of breath from having to deep scrub every surface in the house, with Sam standing over this shoulder for most of it to tell him if he was doing a subpar job at it.

"Well think about this next time you want to throw a missive party/gangbang." They sat down across from one another.

"I just wanted to have some friends over the sex wasn't my idea, it was Cas's!" Dean stopped himself there. It was wrong to accuse Cas like that, to claim it was all his fault when Dean wasn't sure about it. At the same time it logically had to be Cas, he knew he'd never agree to something like that on his own.

"Have you put any thought into him?" Clearly he had, he just accused Cas of being the perpetrator of last nights fiasco.

"Into Cas?"

"Into taking a break in your relationship. You aren't on the same page so some space will help you settle your nerves. Its best to distance yourself from whatever caused an issue or trauma." The venomous lies were accepted as truthful facts so willingly in Dean's vulnerable state.

"I just....I'm worried he'll think I'm breaking up with him. And I guess it might come to that, but I still feel like the option should be open, you know?"

"I could do it for you."

"Huh?"

"Give me your phone, and I'll text Cas saying you want to take a break for a little while. You're still feeling off kilter, but I'm relaxed so I'll be more calm if I text Cas." 

"I'm not a mental case!" Dean shouted.

"I never said that, what I'm saying is that you're stressed and you need to relax. If you do this while upset Cas will think you're asking to break up with him."

Dean's whole posture and demeanor changed with that. "Do you really think he'll react like that."

"It seems more likely that he will than that he won't, Dean. I'm only trying to help you." Though not in the way you think I am.

"Okay, I'll give you my phone after lunch. Let's eat."

"Okay, Dean."

Sandwiches were eaten in silence with Dean finishing off and leaving his plate in the sink before he walked to his room to take his phone off the charger.

"Here."

"Thanks, Dean."

"Just remember to be kind."

"I know Dean, I know." But knowing what he wanted and acting on it were two entirely different things.

He started by sending Cas a text message that said. "Hey Cas I think we should take a break."

The, "If that's what you want." Cas used when he responded pissed him off and set up a perfect way to lie to Dean.

After that he sent more than a dozen messages that would piss off Cas and leave him running for the hills, and the litany of angry texts Cas sent back were proof of it. Until it was punctuated with a "Never talk to me again."

Then Sam deleted everything, but his first text to Cas and his response to it. Following it up with blocking the number so in case Cas ever wanted to apologize Dean would never even see it. Now his roommate was perfectly single and he had all the time he needed to finish what he'd started.

He walking in on Dean as he had his face close to the ground while he scrubbed at a particularly difficult beer stain. Sam didnt announce his presence at first with the site of that ass high in the air, welcoming him to pull down those boxers and push right on in. So many chances to fuck Dean and he was denying himself until later. But he could indulge just a little bit here and how. Sam patted Dean's plush ass as he announced his presence. "Here's your phone back."

He looked startled, but he was more preoccupied with his phone and Cas than with Sam's personal space issues. "What did you say?"

"You can read it for yourself." Well, the parts that are left of it.

He scanned over the two short messages. "Is that all he said?"

"Yeah, my guess is that he's respecting your personal space."

"Maybe I should send him another message letting him know that we aren't completely through together. There's still a chance to try again."

Sam pushed the phone down out of his line of sight. "That'll just make you look like you don't really want space, and it'll send a conflicting message to Cas. Just let things be for now and wait."

"Kay. I'll go put my phone up and then get back to the floor."

"If you work quickly you might manage to clean the whole house before tomorrow."

"That doesn't sound nearly as good as you act like it is."

"Whatever."

For the rest of the day Sam let his shorts hang even lower on his body. Dean knew what his cock looked like and presenting it like this in such a passively suggestive manner would make it fill Dean's thoughts without him even realizing it.

....

Sam thought that Sunday wouldn't be beneficial to moving their relationship forward until Dean entered his bedroom after dinner.

"Hey, Sammy."

"Yes?" Dean hadn't even knocked which was infuriating, but he also looked adorable shy for some reason, so he could let it slide this once.

"Thanks again for helping me yesterday."

"I already told you I was fine with helping." Happy to watch you squirm while the restraints were removed.

"You seemed to know a lot about a relationship involving things like that and I-I was wondering if you could help me understand it." I'm a fool for doing this, it'll just drive Sam away.

Dean was asking about BDSM. There were about a thousand different ways to reaction to this accompanied by hundreds of things that sam wanted to do but he settled on being calm in his answer. "Its about trust, Dean." It was vague enough to not give away anything.

"Trust?"

"Yeah, trusting someone to do something your not sure you'll like, but they think it can either be good for you or help you in some way. It's a transfer of the decision making power." Controlling you and making you mine.

"I don't understand."

"How about I show you with an example, will that make it easier? Something simple and mundane that doesn't mean much, but can still leave an impact. That good."

"I think so."

"Okay then. Tomorrow I'll pick what underwear you wear to work."

"The fuck?"

"Dean, I just told you this is about trust and you need to trust me to do this. It won't affect anything at all; its just to help you understand the way things work."

"Oh, alright." He was hesitant. Sam would need to stop that hesitation. 

"I'll just leave a pair of underwear on the bathroom doorknob while you're taking your shower and you can just grab them and slip 'em on. Okay?"

"Okay. Well I'm gunna go to bed then."

"Sleep well Dean."

"Night, bitch."

"Jerk."

....

Dean was taking his morning shower while Sam was out on his morning jog. He had forgotten about their agreement until he opened the bathroom door and saw a pair of black briefs hanging on the handle. He didnt own a pair of black briefs so that meant this pair belonged to Sam.

With his towel around his hips and the underwear in his fist he stalked over to Sam's door and began pounding on it until he answered. 

Apparently he picked the absolute worst moment to confront Sam, because he must have been in the middle of changing. When Sam answerd the door he did so in only a sheer white thong that did nothing to hide his erect cock.

"What is it Dean?"

Momentarily he had forgotten that. His reason for banging on Sam's door. Suddenly whatever it was didn't matter becuase the reality of seeing Sam's cock again was driving him wild.

"Dean what do you want?" 

"Oh, yeah, um what are these." He shook his hand with the briefs in them while the other one tightened its hold on the towel.

"You agreed to let me pick out your underwear, remember? So I chose those."

"I assumed you would have picked something that belonged to me not one of your weird things."

He was sick of this childish whining and was going to settle things now. "I'll say it again. You agreed to let me pick out you underwear. Nowhere did I agree that it would come from your drawer. I couldn't find a pair of yours that I liked so I went with a pair of mine. Now get dressed of you'll be late for work. Understood?!" Dean may have been older than him by four years but Sam had several inches of height on, so he could easily act like the superior one in their relationship.

"Fine." It was sarcastic but with a meekness to it. He lost the fight and was going to let Sam have his way.

Sam never got to see Dean get dressed but he saw him walk out the door in his coveralls, so there was no way to peek and see if he followed order. Sincerely he did hope Dean wore those briefs. Unbeknownst to Dean, Sam had used it as a cum rag two times the prior night, by this point it would have dried but Sam knew about it and that's what really mattered.

Later that night Sam got home early, having learned that Dean was staying late at the auto shot to finish up on some old car. The finer points didnt matter but what was important is that he would be able to stop Dean the second he stepped into the house.

A casserole had been in the oven for twenty minutes when the garage door opened and Dean came I to the house. Sam stopped him before he had the chance to enter him room.

"Let me see 'em, Dean."

"See what?"

"Let me see that your wearing your briefs like you're supposed to."

"The fuck you asking for." He started shouting.

"So I know you followed through on your end of things." It was quickly turning into a screaming match.

"Don't you keep talking about trust and shit? Can't you just fucking trust me?"

"I want to but you were so apprehensive to it this morning that I need to make sure you were listening. If you need me to explain something again I can, because we need to fucking communicate to trust each other."

"Well I did it so fucking believe me."

"If you did it them you shouldn't mind proving to me that you did it."

"Fine." Dean pulled down the zipper in a flash and yanked his arms out of the sleeves of his coveralls. Then the shoved it down around his knees and pulled up his shirt exposing all of his torso and just a little bit of his nipples. "Happy now?"

Sam was mesmerized by the way Dean looked. His uniform pooling around his knees while his hands clutched at the fabric of his shirt that he held up near his chest. If he craned his neck just a bit he could catch how Dean's ass was stretching the back of his underwear. He was more generously proportioned in that area so the fabric clung tighter too him and put him on display. It put Sam in a nicer, more understanding mood.

"Yeah, that's better. See Dean it wasn't so hard, I just needed you to reassure me that you could listen. This seems like a lot that doesn't make sense right now but give it a while and I'll think itll help you."

"Sheesh, no need to get all preachy and sentimental on me, Sammy." 

"Dinner should be done soon. Just chicken casserole, so you should still like it even if there's no beef in it. Get changed and wash your hands."

"Hm." And Dean turned around with his shirt lowered but his pants still down around his knee caps and he half walked, half waddled to his room. Sam didn't know if it was intentional of unintentional that he was showing off his ass like that, but he was greatful for it all the same. His rear end looked good.

....

That was it for two more days. Sam would hang a pair of briefs on the doorknob to the bathroom and Dean would wear them to work, come home, and show Sam that he did in fact wear them to work as he agreed to do. He was still unaware that they were each used as a cum rag while Sam masturbated to the images of Dean he was able to glimpse that day.

On Wednesday Sam was privy to more than just some glimpses. He'd been going around the house in just briefs or a thong himself whenever Dean came home at night to encourage him to strip down as well. His erect dick had a habit of not so accidentally slipping out right when Dean would look at him. He always excused himself and tucked him back into his underwear while still making eye contact with him.

Dean finally took the hint and when Sam called him to dinner on Wednesday he came into the kitchen in the white briefs Sam gave him that morning. They were actually sheer in the back but Dean wouldn't ever notice it on his own. The slow drawl of seduction was starting to take affect and Sam could kick things up a notch now.

"So Dean are you starting to get the point of giving up power and trusting someone." He knew the head of his dick was sticking out and he knew Dean's eyes were staring at it.

"Um, uh.... N-not really. I'm kinda just wearing different underwear."

"But do you like the different underwear? Dont you think it's better than what you used to wear?" He was leading Dean to draw the conclusion he wanted him to.

He took the bait. "Yeah, they're softer than my boxers, but you coulda just told me to try these." He sat down at the dinner table. A chicken sandwich and corn on the plate in front of him.

"Well how about we try something more Dean. Add another thing to your morning routine." Sam stepped behind Dean and started working his fingers into his shoulders. Dean had a hard time saying no to others, even more so when they were being kind to him. "Just another small change to help you relax. Remember Dean you said you'd trust me and that involves, letting me do things that you man not like."

"But, w-whay if I'm really worr-OH!" Sam was getting into the knot between his shoulder blades perfectly, like he had practiced this exact movement before.

"If you're worried about something, then we can talk about it, figure out why you're worried, and move past it. Remember I know what's good for you Dean."

"You do?" His mind was hazy from the arousal he started to feel whenever Sam was around and the massaging of his shoulders.

"Remeber all those things Cas did without asking you Dean. I'd never do that. He doesn't know what's good for you, but I do."

"What if I liked some of those things?"

Certainly not the turn Sam expected but he could work this into his strategy. "We can work those things in if you'd like to, but for now we'll start with something smaller, okay?

Dean lazily nodded his head.

"Alright after dinner I'll put a bottle of lotion on the bathroom counter, every morning after you've dried off from your shower I want you to rub it into your balls but don't jerk off Okay. What will you do Dean?"

"Massage my balls with lotion but dont jerk it." He was palming at his erection without realizing it.

"Nice job Dean. Now eat your dinner."

"Okay, Sammy." With one hand he ate and either the other he toyed with himself. If he ever came too close to coming Sam would give a gentle reminder to focus on his food not his dick.

....

Dean felt weird after his shower. He sat on the toilet and held the bottle that had been on the counter in his hands. The label even advertised softer balls in just days. But he'd never been one to play with his balls. Touching them intention for a long time had never been something he'd done before, but he'd agreed to it so the first time had to start soon or he'd be late for work.

The lotion was on the liquidy side of things and it almost dribbled out of his hand, but he got it under his balls and was thankful that the heat radiating from his shower seemed to warm it up.

His hands worked in unison to get into all the folds and creases. One would stretch the other would rub it in. He also got a little more when he realized she didnt have enough to get this balls completely.

The actions made his cock hard and even with the strong temptation to touch himself he resisted becuase Sam instructed him not to. Sam couldn't actually know if he did or not be he had a feeling that Sam would figure it out somehow.

Sam would know. He had drilled another hole into the wall connecting the bathroom and the garage that gave him a good view of the toilet where Dean was massaging himself. If he ever caught Dean even touching him cock for a second he'd lay so much shame down on him that Dean would admit it and then beg for forgiveness.

Watching him work Sam nearly came in his pants. He was going to be cutting back significantly on his morning runs if he spent all his time watching Dean toy with himself.

When Dean stood up Sam made a dash for his bedroom and dropped his shorts to the floor leaving him in the same thong he'd worn the day he'd "found" Dean on his bed. He anticipated a reaction from Dean this morning since instead of a pair of briefs hanging on the door for him it was instead a jockstrap. 

Friction was inevitable but when there was no knock at his door Sam was hopeful that Dean accepted his lot in life. Though that may have just been him being overly optimistic. He would have to make sure Dean was wearing the jockstrap as soon as he stepped through the door after his shift even if thay required him to leave early to beat Dean home.

He could do it. The firm he worked at adored him and his incredible work ethic and argumentation skills. Managing to wiggle out of one day would be child's play and getting a few more night off would be almost as easy. Dean wouldn't escape his punishment if he had chosen to be deceitful. 

....

as Dean walked through the door it only took one stern look from Sam, and his coveralls were coming down. 

It was just as he'd hoped. Dean's smaller cock looked almost insignificant in the large pouch made to accommodate Sam's larger girth.

"Turn around, Dean." He never asked this of him before but he wanted to stare at that ass on his own time and at his preferred pace, instead of only when he was in the same room as Dean.

"Uh, Sammy."

"Dean." He spoke with no room to argue, so dean turned in a small circle.

Just like he expected that generous ass was stretching the bands of the jockstrap wider and they dug into his flesh. Why Dean ever thought it was a good idea to conceal such a wonderful rear end was a mistake that Sam wasn't going to let him make anymore.

At dinner he gave Dean another massage and his hands drifted down to Dean's lower back, but as he rubbed into it they both nearly came from that alone and he didn't want to destroy their fun prematurely so he ascended to back around his neck, while Dean abandoned his dinner and just openly touched himself.

....

Friday marked one week following his discovery of his roommate in such a vulnerable state, so he chose to celebrate it by pushing Dean's hand out of the way at dinner and instead using his own to bring the man pleasure.

When he reached under the pouch of that day's jockstrap he squeezed Dean's balls, and was happy to find that even after only a few days with the lotion they were already much softer to the touch than they had been before. But, he wanted them to swell up so their sensitivity would be increased whenever he chose to take a riding crop to them. For that to work Dean would need to stop getting himself off as much and he knew a way to do that easily, but for now he would let Dean have this: the last orgasm he may see for sometime.

Sam's large hand made him seem smaller than he really was, that was the way Sam's whole being really effected Dean. His unoccupied hand stroked over his flat stomache. Dean could have had a nice six pack if he only put in the effort, but he was perfect as he was.

With a twist of the wrist as he stroked over the head Dean wa.coming in his hand, and he was too dizzy in his afterglow to see the way Sam licked his cum from his fingers while getting himself off.  
....

Saturday he planted the next seed into Dean's head. "Hey, did you ever get tested for any STDs after the stuff that happened last weekend?"

**Notes for the Chapter:**

> Leave comments. I'm not above groveling, but groveling takes a lot of effort so if you could just go ahead and comment I'd appreciate it.
> 
> There will be actually sex in the next chapter but I needed space to set up what I have planned next.


	3. Chapter 3

**Summary for the Chapter:**

> Sam pulls some medical buffoonery and Dean falls for it.
> 
> Now it's proofread.

**Notes for the Chapter:**

> Like wow I wrote a fuck ton about a catheter, I didnt expect it to turn out this long but that's what happens.

"Did you ever even think about getting tested for STDs?"

"No. I didnt think I needed to."

"Dean you had sex with a ton of guys bareback, do you really think you can just not get tested."

"I was thinking about other things."

"Well look I've got some cups we use for clients back at the firm, and I can take it to the clinic we use to see if you caught anything."

"Do I need to?

"Do you want to have sex without a condom ever again?"

"Fine, I'll do it."

"Okay I've got some in my briefcase so you can do it now."

"Why would you carry those around with you?"

"Suprise drug tests for our clients. A way to provide insurance for ourselves in case our clients snap or something. Just covering all our bases."

....

Pulling off the lie was easy. Sam took the sample to work, dumped it in the trash, and in his free time he worked on some convincing, fake medical documents about Dean's condition.

He didn't have an STD. The only people Dean had sex with in the last year were him and Cas, but Dean didn't know that. He still believed hed been on the receiving end of a massive gangbang where anything might have happened.

That fear could be easily used to manipulate him into believing he had any issue Sam wanted him to think he had. Just a few more small things to buy and Dean would be on his hands and knees begging for mercy.

....

"Dean I got your results back." Sam announced it while walking in through the front door. Dean had beat him home today, but if he knew what was good for him he'd be spending that alone time in his underwear like he would have if Sam had been there the whole time.

"What's it say?" Dean walked in from his room. Only that wonderous pink thong covering him. It fit him and Dean in completely different ways. For him it made his cock seem more immense than it was (even thought it was already the largest he knew of), and on Dean it highlighted how full his thighs were. Again the large pouch dwarfed the size of his cock, making it look petite in its confines.

"Well you dont have any STDs, but you do have a urinary tract infection."

"What am I supposed to do about that."

Sam nodded to the bag he'd been carrying in his hand. "Well I have some antibiotics that should help since we caught it early, but they said the most important way to keep it from spreading is to avoid achieving an orgasm during sexual intercourse, and to avoid urination."

"How the hell do I go without sex and how the fuck am I supposed to survive if I cant piss?"

"You can have sex Dean it's just that you can't cum from it."

"Well then what's the point?"

"I can show you lots of ways to enjoy sex without even thinking about that dick of yours."

Dean was flustered and intimidated, he changed the subject before anything stupid or dangerous could happen. "And what about pissing?"

"I was told that a catheter could be used and there would be no negative effects from it, but they mentioned that trying to go the the bathroom without it just once could jeopardize everything."

"Please explain what that means."

"If just a single time you don't feel like dealing with a catheter and you piss on your own your going to be in a lot of pain." Pain caused by me but the finer details dont matter. "I'll help you insert the catheter and we can see how you like it. Then we can decide if you want to keep one in constantly or if you'd rather swap it out for a sound when you don't need it."

"This seems like a lot just for an infection."

"Your bladder is important and a bad infection can kill you. Now lay down on the couch so I can insert the one I bought for you at the store."

"Alright."

The catheter slipped in painfully, like he wanted it to. This wasn't a thin one and it certainly wasn't a short one. It was one of the largest he could find that still looked medical in its design.

With this shoved into Dean's slit it would be impossible for him to get hard, and as far as he would ever know, he had a supposedly indefinite UTI that prevented him from peeing normally.

There was a valve attached to the tube at the end that prevented anything from flowing out of it. It could be loosened and tightened to allow for several levels of flow into the bag. Sam set it to the lowest trickle setting and watched as the clear liquid slid from Dean's slit as he moaned. With sounds like that slipping from his mouth Sam saw no reason to ever increase the flow of it. Dean would feel like he was constantly pissing his pants with this working as it did, and it created another step of reliance on him.

"Does out feel good Dean?"

"It feels weird, like it's happening without me doing any of the work."

"After dinner tell me how you feel about it. If you think itll be uncomfortable after having it in for a long time you can wear a sound to work at the garage, but remember if you do that then you can't pee the whole time you're at work."

"Oh."

"I'll get you some water, Dean." Perfect, wonderfully perfect. This was going swimmingly with Dean surrendering something like this over to him so easily. 

The glass of water he filled was a liter in size with a hefty dose of a diuretic added into it to put more pressure behind Dean's bladder. The pain would build up there and with the slow crawl of the catheter it would take hours to relieve it, by then Sam would have him drink a whole new glass.

While Dean was watching tv Sam watched him and the way the bag slowly filled up, until he had to replace it with another one when the first became full.

The bag wash trashed and Sam went to his room to grab a fleshlight, one of his largest ones. Actually it was the only one capable of taking his entire dick into it. With it he brought a bottle of cherry lube and two nipple clamps for what he had in store for Dean.

Sam sat in the chair with his handfull of supplies on the end table next to him. Dean still wasn't looking at him so he would just have to draw his attention with some noise. He uncapped the lube and squired a hefty amount of it into the fleshlight. This would go to waste if things went the way he wanted, but it would still be worth it.

Easing it over his cock letting the loud squelch of it resonate in the living room, Sam softly moaned in exaggerated joy. Dean finally turned his head and his pupils were blown wide, making no attempt to look away from where Sam's hard cock was being buried inside of the fleshlight or disguise his open staring from the other man. 

"Enjoying the show Dean." He settled it down to the base of his cock and the pulled it up. Changing directions created an obscene sound of the lube moving.

"Sammy, that's no fair. You're gunna get off rght next to me when I can't even touch my dick? Low blow, dude." He still didn't look away too mesmerized by that monster cock he'd gotten to suck on before. 

Sam started to lightly pant. It felt good but not as good as he was letting on. That didn't matter to him as much as getting Dean over there on his knees. "Dont whine. There's plenty of ways to enjoy yourself without touching your cock, Dean."

"Yeah right asshole."

Dean came over as fast as he could carrying the bag in his hand during the frantic steps. He only moved onto Sam's lap when when he was pulled down, setting his baggie on the floor and the fleshlight serving as the only barrier between his soft cock and Sam's hard one.

"Alright Dean I need to ask again, do you trust me?"

"Yeah, Sammy, fuck. Just do something." Without even being hard he felt like there was lust shooting through his veins and he needed to get it out of his system as soon as possible. Even if he didn't rely get off, whatever Sam had planned would have to help him.

Sam pulled up the bottle of lube and nipple clamps from the floor. Dean knew what all of it was, he remembered waking up to the feeling on his nipples being on fire from the pinching sensation they gave him, but these ones didnt seem nearly as intimidating to him. If only he knew these were the same ones he woken up with on that Saturday morning. 

"Now Dean, I'm going to put a little lube on your nipples so they dont get dried out and then I'll put the clamps on them. Your job is to be quiet until I'm finished. Once they're both on and secure you can make all the sounds you like, but until then I don't want to hear a peep from you."

He nodded, already preparing himself to stay perfectly silent.

Sam squirted some of the lube onto his fingers and began to pinch and toy with Dean's nipples. The lube was only about room temperature, so while he wasn't going to get those yelps he wanted out of Dean that he could have achieved with cold lube, Dean's nipples were extremely sensitive, so regardless he would still have a satisfying reaction to look forward to.

He twisted and tugged on them relentlessly. Dean wouldn't question his actions, because that would entail speaking and then he would have to recieve a punishment so, Sam was free to do as he pleased. And when he had worked the lune into Dean's skin like a lotion he just went back and got some more of it. Once that was done he grabbed the nipple clamps.

They were opened simultaneously and snapped on at the same time as well. Sam was impressed by Dean's resolve. Even when his nipples were being manhandled the loudest sound he made was a rough naisal exhale. He had made it to the end of the process so it was time to throw him a bone, if only a minuscule one.

"Okay Dean you can talk now. How does it feel?"

"Oh, God Sammy. They ache and I feel like I could cum right now but I'm not even hard and it hurts." He was shaking slightly.

"Well I did say I would show you how to feel good without even cuming, do you still want me to show you?" Even if Dean had chosen to say no Sam would have guilted him into accepting anyway, but the illusion of choice was important to getting under Dean's skin and into his ass.

"P-Please."

"Okay, Dean. I'll help you. First get down on your knees for me."

Watching Dean ease himself onto the floor was amusing in it's own right. Dean was being so careful in his movements as if just flexing his arm too suddenly would jostle the clamps and send him reeling in agony. With a gently shove from Sam he made it to the ground and Sam pulled off the fleshlight making sure Dean's eyes were trained onto his slowly released cock.

"Now Dean, I'll need you to lick me clean of all this lube first, then I want you to take me as deep as you can into your throat and swallow around me, can you do that." Nornally giving instructions for a blowjob would ruin it. The best part of one was the surprise at how your partner would pleasure you next, but it would be made up for in how Dean perfectly followed his instructions like a good little bitch.

Dean's mouth came forward, starting at Sam's glistening balls and doing one large lick up the bottom of his cock, all the way to the head, until the popped off and repeated it again slightly to the side. He went on like that, occasionally moving to kitten licks to get the finer parts cleaned off. Sam was halfway to an orgams just by that but it wasn't like he was in it for the long game with this round specifically.

Without having to be told to transition Dean grabbed Sam's cock and fed the head into bis mouth, making it more than halfway down before he had to stop as it bumped the back of his throat, illiciitng some hatch gargling sounds as he choked on it.

"Swallow, Dean."

He tried, god he had tried but it was weak and pathetic. Not underwhelming as Sam fully expected Dean to be subpar in this area but he could still feel disappointment. He grabbed that brown hair and forced him back, choking him again.

"Dean, that was fucking pathetic, I expect better from you in the future. Now, use your hand to get me off and I'll come across you face. Maybe if you do that well I'll forgive you."

Dean's eyes were wide and brimming with tears, a few even fell beigre he reached forward and used both hands to massage Sam's cock. He was silently begging for forgiveness in the action. Hoping that having his face painted with cum would be penance for his mistake. And soon it washappening. Sam spurting in thick globs between those green eyes.

Watching it drip down Dean's lashes was worth the effort.

....

"Hey, Sammy you for got to put underwear on the door for me." God, he wanted to blow Sam right there. Would he have even tried to stop him? What was the harm in a sudden morning blowjob. His cock looked so good wrapped up in his sweaty jockstrap. There was never a time he'd seen Sam's cock when it wasn't hard and he was almost envious of it, something big like that dangling between his legs. If Dean had it he would have been so vain.

And now that great cock was uncovered as Sam removed his jockstrap leaving his lower half bare, and the article of clothing was theist in his direction. "Here."

Sam's used sweaty jockstrap from his morning run. That's what our was going to wear to work today, it was going to be impossible to focus now. Just holding it in his fist he could feel the moisture in it from the sweat that had dripped down Sam's balls and even with the other man standing right there he lifted it to his nose and took a deep breath. The inhale carried with it that potent musk he got to enjoy whenever Sam gave him the pleasure of giving oral, or during those secret times he would go to the laundry room and hold Sam's underwear to his nose, while touching him dick. He'd never managed to get off on it, Sam wouldn't be happy with him if he did but the pleasure still clouded his mind. All those times were nothing in comparison to the fresh scent he had now, never before had it been quite so potent.

"Dean, you can smell the real thing after work. Doesn't that sound much better? Getting to shove your face into my crotch all night. We can even share a bed so you don't have to stop when I go to sleep."

"Really?"

"Yes Dean, now hurry alone before is use your ass and we both end up late to work. And remeber you cant remove the catheter for any reason."

"I gotcha."

....

Work was a new experience for him, but to anyone else around him it was absolutely nothing special. But, his coworkers didn't have an extra long (and unknown to him extra wide) catheter shoved inside of them. Dean had woken up when Sam removed the old one and slipped the new one in. When he complained about feelings of pain and discomfort, Sam simply dismissed his whining and said that he was still adjusting to it.

There was going to be a lot of adjusting when it came to the catheter actually, since Sam planned on working Dean open with larger and larger ones until his urethra was gaping open and aching to be filled. Preferably this would end with Dean forgetting how to even pee naturally after relying on the catheter for so long, but that was something partially outside of Sam's control. 

The new catheter had a shorter tube connecting it to a bad attached to Dean's hip. He could have gone with a standard bag that wrapped around the waist like a fanny pack, but this way Dean would feel the warm heat of his urine trickling out of him so shamefully.

....

Dean beat Sam home again, and he stripped down to just his jockstrap with the tube from his catheter sticking out to the side and the almost full bag on his leg. Sam made no mention of working late tonight so hopefully he would return home soon to swap him over to another bag. If the one he currently had became filled to the brim be didn't known what he would do, because no matter what the catheter never stopped pulling liquid from his dick.

He wanted to do something naught and scandalous while he was alone. Maybe sniff Sam's dirty laundry hamper? He was starting to think he could get hard and cum from the sensation. The scent of it drove him wild in it's own way. It would have been easy and Sam would never know, but it would be wrong to do that to Sam who was being so king to him, and if he could just wait a little while longer then Sam would be home himself. Plus Sam constantly reminded him of the dangers of him achieving an orgasm, but it had been too long since his last one.

That morning he had promised Dean that he would have the opportunity to sniff his cock and balls, drowning himself in that musk. Hopefully Sam spend his day sweating in his suit so it would be extra potent. So he waited.

....

Opening the door to find Dean splayed out on the couch was a welcome sight, but what he said next was even better.

"Hey Sammy can you go ahead and switch out the bags, this one's nearly full. Also, can I sniff your cock now, you said I could this morning and I'm sick of waiting."

"Of course, Dean. Just let me get undressed and we can get right on that." Sam didn't go to his bedroom to change he just dropped his briefcase by the door and started stripping there. "Actually Dean, I know that I said you could smell my crotch after I got home, but wouldn't you rather I just fuck you. You can even smell my thong while I'm at it, I've been sweating all day from thinking about you, so it should he good.'

"Please, fuck me." He was desperate after just the few worlds. Sam had been winding him up for days so it was simple to finally push him over the edge into desperation.

"Alright it can be your reward for being so good." He was going to destroy Dean. Working his ass open until he would never be able to close all the way again, shove that thong so far down his throat that, even if he tried the taste would never leave his mouth. He could already picture the way a cloudy liquid would fill the catheter as he brought Dean to a prostate orgasm, that would do nothing to quench his lust. Then he would have Dean spend the night in his bed and enjoy using him again and again until the sun had finally risen.

And then maybe tomorrow he would try a spider gag and fuck Dean's throat until he couldn't even moan properly.

**Notes for the Chapter:**

> Please comment. I beg of you.
> 
> Also I'm on twitter. @MoonlightIcarus 
> 
> That's just like me to join a social media platform as its slowly dying out. Oh the mistakes I have made.

**Author's Note:**

> Never tied something like this before. Dont plan on doing something like it in the future.
> 
> Tell me what you thought. I might do a second chapter if people ask for it.
> 
> If you need a reference for how Sam was dressed here's a link that gave me the idea for it. https://twitter.com/yuufreak/status/1136425376568053760?s=09


End file.
